Gary Smith on intimacy and connecting with subjects: "Any uneasiness you bring is going to cost you dearly"

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On the last day of the Mayborn Conference, Sports Illustrated’s Gary Smith read from and discussed “Shadow of a Nation,” his 1991 story about a Crow basketball player named Jonathan Takes Enemy. Smith has been at Sports Illustrated for nearly two decades, winning more National Magazine Awards than any other writer. He’s known for his ability to connect with his subjects, and so we were very interested in the answer he gave to a question about how he enters others’ worlds as an outsider and develops intimacy:

To become a longform writer and to kind of immerse yourself in different worlds, it’s almost like a double-railed track. Not only do you grow as a writer, but that other rail of the track is huge. Part of it is something you’re developing – some sense of self, getting a little more at ease in your own flesh and bones. So much of what happens in the interactions between you as the writer and the subject hinges on their trust in you, their confidence in you. And so much of that hinges on how comfortable you are. Any uneasiness you bring is going to cost you dearly.

I’ve sensed that and felt it and seen it as the years go by. The more at ease I became, the more the trust grew in that interaction, the more goods, the more treasure came back. It’s almost like you need to be very aware of both sides of that railroad track. If one is lagging behind the other, you’re going to really shortchange yourself in everything you get as a writer. That’s not the reason to do it — there are a zillion other better reasons to go on that trip. But that’s one of the biggest benefits of it.

As you’re walking as an outsider into these worlds all the time, how comfortable are you in doing that? If they feel your uneasiness, how easy are they going to feel about handing you their most intimate stuff to write about?

There’s almost an equivalence to that interaction, so the more they sense that you’re really there just to understand rather than judge is huge in how much they’re going to start giving … When you’re more relaxed, you listen, and you’re ready to flow with what’s being said and to hear something that’s sparking off three or four other questions in your mind. It’s because your mind is more relaxed; it’s not tense and tight and worried about getting that next question on your checklist.

When it goes from an interview to a conversation, that’s when things really start to happen in that interaction … but it’s not there at the beginning, I can guarantee you. When I was 25 years old doing this, I was nervous as a cat and worried and sometimes in awe of the person I was interviewing. It’s all just time, putting in time, and also really, you wanting to grow as a person and to throw yourself into circumstances that aren’t always the most comfortable right off.

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Smith’s ability to get inside his subjects’ lives and ways of seeing the world is legendary, and so I found myself curious if he’d ever encountered a subject with whom he felt unable to connect, and if so, how he had handled writing the story. I caught up with him the night before his talk and put the question to him. He mentioned that Tiger Woods had spent a good part of their interview time watching Sports Center, but seemed unable to recall anyone for whom he just hadn’t felt empathy. Here’s what he had to say about it:

If I can’t get there, I shouldn’t even start writing. There should be some feeling for the human condition, in a way, and so if I can’t get there at all, then it’s like trespassing to write. If I’m going to write about pretty intimate stuff, I shouldn’t go there unless I can treat it with that kind of feeling.

I’ve started into stories and done a lot of research and then pulled out. But once I meet the person, I’m pretty dogged about just thinking “I’m going to find some connection and find my way into this person’s world and understand it and try to grasp it and render it.” Even if there’s a lot of banging my head against the wall, I’ll just keep coming back at it and at it. That’s what I’ve found. Maybe it’s not smart, but that’s what I’ve done.

It’s funny, because that whole idea of crossing that abyss to the other, there’s something under it that’s compelling to me, I would have to guess. Why else would I be doing this so much, so long, and so feverishly for so many years?